Pyridine → 2-Chloro-N-(1,4-dioxo-1,2,3,4-tetrahydrophthalazine-5-yl)acetamide

HRID 241486ノート

反応式

HRID 241486 の反応式
[CH:1]1[CH:6]=[C:5]([NH2:7])[C:4]2[C:8]([NH:10][NH:11][C:12](=[O:13])[C:3]=2[CH:2]=1)=[O:9].[Cl:14][CH2:15][C:16](Cl)=[O:17].N1C=CC=CC=1>CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O>[Cl:14][CH2:15][C:16]([NH:7][C:5]1[CH:6]=[CH:1][CH:2]=[C:3]2[C:4]=1[C:8](=[O:9])[NH:10][NH:11][C:12]2=[O:13])=[O:17]

参加物

5

反応物 3

HCID 1049PyridineHCID 6577Chloroacetyl chlorideHCID 10638Luminol

生成物 1

HCID 543576732-Chloro-N-(1,4-dioxo-1,2,3,4-tetrahydrophthalazine-5-yl)acetamide

試薬・触媒・溶媒 1

HCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl ester溶媒

実験手順

Luminol (1.55 g; 8.75 mmol) was reacted with 2-chloro-acetylchloride (1.24 g; 10.99 mmol), in the presence of pyridine (1.07 g, 13.6 mmol) in acetic:acid (45 ml). Contents were stirred and refluxed for 1 h, allowed to cool to RT, and transferred to a refrigerator for precipitation of the product to obtain 2-Chloro-N-(1,4-dioxo-1,2,3,4-tetrahydrophthalazine-5-yl)acetamide. Thereafter, acetic acid (20 ml) was added to the cold precipitates prior to filtration (for uniform transfer into the filtration unit). Finally, precipitates were filtered, washed with methylene chloride (three times) and dried under vacuum to yield 2-Chloro-N-(1,4-dioxo-1,2,3,4-tetrahydrophthalazine-5-yl)acetamide (1.6 g; 6324 mmol; 72.2%). 1H NMR (300 MHz, DMSO-d6) δ: 8.82-8.87 (t, 1H), 7.71-7.89 (dd, 1H), 7.61-7.69 (dd, 1H), 4.34 (s, 2H), 2.16 (s, 3H, Methyl for Acetic Acid); ESMS: Calcd for C10H8ClN3O3: 253.0, Found, 253.8.

後処理

  1. temperaturerefluxed for 1 h
  2. customtransferred to a refrigerator for precipitation of the product

出典と根拠

ORDレコード
ord-1fe4a8b7ba31481dbb6c6ea70e14ba5d
出典データセット
uspto-grants-2014_02
特許番号
US08652442B2

反応ノート

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